Cheltenham Vacation Packages

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Your Cheltenham Vacation

Say goodbye to the worries of planning and hello to a Cheltenham vacation package. With everything organized before you go, you can focus on discovering the best of this city, starting with Montpellier, which is good for bars and pubs, dining and cafes. Make your trip to Cheltenham even more fun and exciting by going sightseeing. Cheltenham Racecourse, Sudeley Castle and Cheltenham Town Hall are some of the top attractions worth exploring. Whoever you're heading away with and whatever your bank balance, your dream Cheltenham vacation is just clicks away with Expedia.

Top Cheltenham Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Leonardo Hotel Cheltenham

Leonardo Hotel Cheltenham

4 out of 5
Price was CA $1,474, price is now CA $1,266 per person
CA $1,266
per person
Oct 14 - Oct 20
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Birmingham (BHX)
8.4/10 Very Good! (1,001 reviews)
Staff very helpfulband apologetic for very slow service when ordering food and drinks.

Reviewed on Aug. 13, 2025

Charles Hope Birmingham Westside

Charles Hope Birmingham Westside

3.5 out of 5
Westside
Price was CA $2,346, price is now CA $1,833 per person
CA $1,833
per person
Oct 25 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Birmingham (BHX)
No reviews
Cozy Cotswolds Retreat in Dursley

Cozy Cotswolds Retreat in Dursley

2 out of 5
Price was CA $1,895, price is now CA $1,590 per person
CA $1,590
per person
Oct 14 - Oct 20
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Birmingham (BHX)
No reviews
The Lion Inn

The Lion Inn

4 out of 5
Price was CA $2,308, price is now CA $1,963 per person
CA $1,963
per person
Oct 14 - Oct 20
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Birmingham (BHX)
8.6/10 Excellent! (110 reviews)
We loved our stay at The Lion Inn in Winchcombe! Super convenient location with easy parking, delicious on site dining, and walkable to shopping, trails, the castle and more!

Reviewed on Jun. 18, 2025

Ellenborough Park

Ellenborough Park

5 out of 5
Price was CA $2,706, price is now CA $2,330 per person
CA $2,330
per person
Oct 14 - Oct 20
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Birmingham (BHX)
9/10 Wonderful! (535 reviews)
Absolutely beautiful hotel grounds with good and relaxing vibes! The swing at the garden is a place you shouldn’t miss, the view is gorgeous indeed! I’m staying with kids and surprisingly they enjoyed the stay a lot! Staff are wonderful, polite and helpful, thank you Grace and John at the reception who made our stay even more memorable! Will definitely recommend this place and I hope I’d be back again one day!!

Reviewed on Aug. 14, 2025

Ready to book your vacation to Cheltenham?

 

Choose your dates

Cheltenham Hotel Deals

Cheltenham Chase Hotel & Spa

Cheltenham Chase Hotel & Spa

4 out of 5
Shurdington Road, Brockworth, Cheltenham, England
Fully refundableReserve now, pay when you stay
The price is CA $119 per night from Aug 21 to Aug 22
CA $119
CA $143 total
Aug 21 - Aug 22
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
"Great value for money"

Reviewed on Aug. 17, 2025

Cheltenham Chase Hotel & Spa
Leonardo Hotel Cheltenham

Leonardo Hotel Cheltenham

4 out of 5
Gloucester Road, Cheltenham, England
Fully refundableReserve now, pay when you stay
The price is CA $119 per night from Aug 31 to Sep 1
CA $119
CA $143 total
Aug 31 - Sep 1
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
"Amazing reception, great gym, perfect breakfast, but no air con and pillow (both available) quite big."

Reviewed on Aug. 12, 2025

Leonardo Hotel Cheltenham
Queens Hotel Cheltenham

Queens Hotel Cheltenham

4 out of 5
The Promenade, Cheltenham, England
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from Aug 21 to Aug 22
CA $173
CA $207 total
Aug 21 - Aug 22
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
"Comfortable bed Unfortunately the air conditioning did not seem to be working ; there were no clear instructions how to use it so the room was like an oven"

Reviewed on Aug. 17, 2025

Queens Hotel Cheltenham
See all 1,119 properties in Cheltenham
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Cheltenham

Sudeley Castle featuring a church or cathedral, a park and heritage architecture

Sudeley Castle

Uncover centuries of royal history amid the halls, gardens and art exhibitions of this 15th-century castle set in the shadow of the Cotswold Hills.

Sudeley Castle
The Model Village which includes interior views

The Model Village

Walk amid a scale model replica of the shops, houses and historic landmarks that were present in Bourton-on-the-Water during the 1930s.

The Model Village
Chedworth Roman Villa which includes a pond, heritage elements and a house

Chedworth Roman Villa

Roman-British history comes to life at the bathhouses, mosaics and museum of this ancient villa set in the picturesque Cotswold countryside.

Chedworth Roman Villa

What to do in Cheltenham

Classic Cotswolds – Online Self-Guided Road Trip Plan

Classic Cotswolds – Online Self-Guided Road Trip Plan

CA $24
per traveller
Classic Cotswolds – Online Self-Guided Road Trip Plan
Bourton-on-the-Water

Private One Day Luxury Tour of The Cotswolds

CA $1,738
per traveller
Private One Day Luxury Tour of The Cotswolds
Private Full Day Tour to Cotswolds from London

Private Full Day Tour to Cotswolds from London

CA $4,575
per adult
Private Full Day Tour to Cotswolds from London
See all activities in Cheltenham

Frequently asked questions

How much does a Cheltenham vacation package cost?
You can grab a vacation package to this destination from CA $1,266 on Expedia. But how much your vacation to Cheltenham costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Cheltenham?
December, January and February are great times to search for cheap Cheltenham vacation packages. Opting to travel in less busy periods means you'll typically find lower prices on accommodations and flights.
How many days is enough for Cheltenham?
Allow around 2 days for your Cheltenham vacation if you want to take in everything that makes this place unique. Wander around popular neighbourhoods, including Barnwood and Shurdington. Then head to the top attractions such as Cheltenham Town Hall and Pittville Park. With a good itinerary, you can keep busy with room for some downtime too. Want to travel beyond Cheltenham? Consider fitting in an excursion or two.
Is it worth booking a vacation package to Cheltenham?
It's easy to see why a Cheltenham vacation is on the must-do list of many travellers. Popular attractions like Cheltenham Racecourse are just the beginning of what you can explore here.
How to find the best Cheltenham package deals?
Landing a cheap Cheltenham package deal is easy with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget range, apply a couple of filters and see what's available. You can fine-tune your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to view the most economical Cheltenham package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Cheltenham vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and hotels individually. Better still, you can personalize your Cheltenham escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Cheltenham?
Score incredible bargains by reserving your flights early with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for an impromptu Cheltenham escape.
How to plan a trip to Cheltenham?

  1. Pick your travel dates: The things you'd like to do in Cheltenham and your preferred season can help you decide when to travel.
  2. Figure out your budget: Make sure you have enough money to pay for everything from dining out and transportation to activities and airfares. Your accommodations will likely be the biggest expense during your trip to Cheltenham.
  3. Determine how many days away: Start by making a list of all the attractions and activities you'd like to get to in Cheltenham. Then, estimate how long you'll need at each, including any travel time.
  4. Combine your accommodations and airfare: After you've settled on your trip dates and duration, book the perfect Cheltenham vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.